Middlebury Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Middlebury
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
฿3,550
฿3,976 total
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (1,009 reviews)
"Great staff. Very clean, worth the price."
Reviewed on 16 Aug 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
฿3,908
฿4,377 total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"Clean and comfortable room and excellent breakfast choices"
Reviewed on 13 Aug 2026
Farmstead Inn & Conference Center
370 S Van Buren St Shipshewana IN
Fully refundableReserve now, pay when you stay
฿4,353
฿5,006 total
13 Sept - 14 Sept
includes taxes & fees
9.6/10 Exceptional! (1,124 reviews)
"Disappointing the hot tub was not available. Best breakfast ever"
Reviewed on 16 Aug 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Middlebury attractions
Stone Lake
This spring-fed Indiana lake offers pristine waters for fishing enthusiasts seeking bass and bluegill. Enjoy a peaceful morning paddle across its reflective surface where motorboats maintain respectful speeds.
Deutsch Kase Haus
9.2/10 (39 reviews)
This family-owned cheese factory showcased award-winning Colby and Colby-Jack varieties through viewing windows. Visitors could sample fresh cheese curds and browse Amish-made products in its rustic setting.
Meadow Valley Golf Club
Set amid Indiana's Amish countryside, Meadow Valley Golf Club challenges players with undulating greens and strategic water hazards. Reserve an early tee time to experience the tranquil beauty of this top-ranked course.
Middlebury Public Library
The Middlebury Public Library offers more than books—it's a community hub with unique lending items like telescopes and museum passes. Browse their collection or join one of their engaging programmes for all ages.
Hunter Lake
Hunter Lake offers a peaceful retreat for fishing and boating, surrounded by lush Indiana greenery. Pack a picnic to enjoy by the tranquil shoreline while watching local wildlife in their natural habitat.
Middlebury Community Historical
You can spend an afternoon browsing the exhibits at Middlebury Community Historical during your trip to Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Corson Riverwoods County Park
This unique park features a Pollinator Playpath with interactive areas themed around butterflies and bees. Explore giant caterpillar structures and honeycomb hideouts while learning about these essential creatures.
Memorial Park
Memorial Park honours veterans with its WWII memorial, band shell, and charming gazebo. Enjoy the serene grounds during community festivals or bring a picnic to experience small-town Indiana at its finest.
Frequently asked questions
How much does a Middlebury holiday package cost?
You can pick up a holiday package to this destination on Expedia. However, how much your holiday to Middlebury costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Middlebury?
If you'd like to score a cheap Middlebury holiday package, consider planning a trip in January, February and November. You'll generally find better rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Middlebury?
The ideal length for your Middlebury holiday depends on what you'd like to see. Generally, a handful of days to a week will give you time to check out all the main sights and discover some hidden gems along the way.
How to find the best Middlebury package deals?
Use Expedia's handy filters to help you find some unbeatable Middlebury package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Middlebury package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Middlebury holiday as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Middlebury?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Middlebury getaway.
How to plan a trip to Middlebury?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Middlebury.
- Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodation will likely be the largest expense during your trip to Middlebury.
- Decide how long to go for: Now that you know more about Middlebury, you can work out the ideal length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
- Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect Middlebury holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
